Tomb Raider II

The Golden Mask

As Lara is enjoying her holiday in Las Vegas, she receives an omnious vision about Winston and then sets out to rescue him.[1]

Tomb Raider III

In Tomb Raider III, Lara can pick up her pistols at the end of the Assault Course. When these are picked up, Winston will appear in a camouflage suit. You can shoot him, and he will raise his tray in defense.

Locking Winston in the Fridge

A fun game that was very popular among the fans was locking Winston in the fridge, as he always followed you. Run into the kitchen. Open the fridge by using the button. Get inside the fridge and wait for Winston to appear. Then quickly run out leaving him and shut the door again. This can be done in Tomb Raider II and Tomb Raider III.

Legend, Anniversary, Underworld

Tomb Raider Legend

Winston returns in Tomb Raider Legend with a biography and an updated appearance, looking much taller and younger and less fragile than before. He also has a more active role in the storyline, providing additional information here and there.

From the official Site

Winston is Lara's butler, and he has served the Crofts for most of his life. He's calm, sophisticated, unflappable, and knows more about Lara and her doings than anyone. He worries about her but he knows how capable she is, and he does nothing to dissuade her from her life's pursuit, and indeed he's just as willing to fetch 9mm ammunition as he is to set out tea service, and he will even toss a few spare ammo clips into her bag without her asking.

Biography

Winston's family has been with the Crofts for generations, and he has been the family butler since he was honorably discharged from the military in his late-twenties; just as his father before him. He moved into Croft Manor to stay as the only live-in staff when his wife died, before Lara was born. He tends to all Lara's household needs, going far beyond the duties of a traditional butler given Lara's unusual lifestyle and pursuits, but he has never disappointed her. His loyalty to Lara, her parents, and Croft Manor is beyond question.

Tomb Raider Anniversary

Even though Winston was not in the original Tomb Raider, he is seen in the Croft Manor. As Lara explores the manor, he is found in several places of the house. If you find 27 Artefacts, you will unlock his biography, which is the same as in Tomb Raider Legend.

Rise of the Tomb Raider

After the death of her mother, Winston took care of Lara whenever her father was on an expedition or too occupied with his research. They played chess together and he wrote letters about her behaviour to her father on a regular basis, e.g. whenever she got into any mischief.

From what Lara remembers of him, he seems to have been a very good friend and mentor, something like a second father, who cared a lot for her. She misses him dearly.

Although he is not seen on screen, his voice can be heard whenever Lara remembers him or reads a letter he wrote.

The Name Jeeves

It seems that the name Jeeves has been given to him by the fans, while the creators at Core Design decided to call him Winston.

Reginald Jeeves is a character in the books of P.G. Wodehouse and has since come to be a common term referring to a butler or valet.